Hydrochloric Acid → HCID 15870845, compound

HRID 1584827Notes

Reaction equation

HRID 1584827 reaction equation
[C:1](OC(=O)C)(=O)C.[CH2:8]([O:15][C:16]([N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:27]3[C:40]([F:41])=[C:39]([N+:42]([O-:44])=[O:43])[C:30]([C:31]([CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:32])=[C:29](F)[C:28]=3[O:46][CH3:47])[CH:24]=2)[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH:48]1([NH2:51])[CH2:50][CH2:49]1.[H-].[Na+].Cl>C([O-])([O-])OCC.C(O)C.C(Cl)Cl.O1CCCC1>[CH2:8]([O:15][C:16]([N:18]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:27]3[C:28]([O:46][CH3:47])=[C:29]4[C:30]([C:31](=[O:32])[C:33]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:1][N:51]4[CH:48]4[CH2:50][CH2:49]4)=[C:39]([N+:42]([O-:44])=[O:43])[C:40]=3[F:41])[CH:24]=2)[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 69828CyclopropylamineHCID 15870855HCID 15870855, compound

Product 1

HCID 15870845HCID 15870845, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 53630039EthylorthoformateSolvent

Procedure

In 0.71 g of ethyl orthoformate and 0.49 g of acetic anhydride was dissolved 0.66 g of ethyl 4-[2-(benzyloxycarbonyl)isoindolin-5-yl]-2,5-difluoro-3-methoxy-6-nitrobenzoylacetate, and the solution was heated under reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue obtained was dissolved in 3.3 ml of ethanol and 2 ml of methylene chloride. To the solution was added 0.08 g of cyclopropylamine, and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue obtained was dissolved in 10 ml of tetrahydrofuran. To the solution was added 0.05 g of 60% sodium hydride, and the resulting mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added 10 ml of 1N hydrochloric acid, and the crystals precipitated were collected by filtration, to obtain 0.33 g of colorless, crystalline ethyl 7-[2-(benzyloxycarbonyl)isoindolin-5-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-nitro-1,4-dihydro-4-oxoquinoline-3-carboxylate.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 30 minutes
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue obtained
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe residue obtained
  7. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  8. customthe crystals precipitated
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-9278687abb024d8d8abcc4c9e80b60a4
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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